Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001)

Advanced Synthesis and Catalysis

Volumn 345, Issue 1-2, 2003, Pages 15-32

  Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Asymmetric hydrogenation; BINAP; Nobel lecture; P ligands; Ruthenium

Indexed keywords

2,2 BIS(DIPHENYLPHOSPHANYL) 1,1' BINAPHTHYL; AGRICULTURAL CHEMICAL; ALPHA (4 FLUOROPHENYL) 4 (5 FLUORO 2 PYRIMIDINYL) 1 PIPERAZINEBUTANOL; ALPHA TOCOPHEROL; AMINO ACID; ANTIINFLAMMATORY AGENT; CARBENE; CITRONELLOL; COPPER COMPLEX; CYCLOPROPANE; DIAMINE; FRAGRANCE; FUNGICIDE; HYDROGEN; KETONE; LEVODOPA; MENTHOL; MORPHINE; NAPHTHYL GROUP; NAPROXEN; ORGANIC COMPOUND; ORGANOMETALLIC COMPOUND; OXAZOLONE; OXIME; PHEROMONE; RUTHENIUM COMPLEX; RUTHENIUM DERIVATIVE; SCHIFF BASE; TRANSITION ELEMENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL HEALTH; ANIMAL PRODUCT; BIOLOGY; CATALYSIS; CHEMICAL BOND; CHEMICAL ENGINEERING; CHEMICAL INDUSTRY; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMISTRY; CHIRALITY; CONFERENCE PAPER; CYCLOPROPANATION; DRUG MANUFACTURE; DRUG SYNTHESIS; ECONOMIC ASPECT; ENVIRONMENTAL PROTECTION; FLAVOR; FUTUROLOGY; HYDROGENATION; HYDROLYSIS; INDUSTRY; LABORATORY; MOLECULE; PARKINSON DISEASE; SCIENCE; SOCIETY; STEREOCHEMISTRY; SYNTHESIS; TECHNOLOGY; THIN LAYER CHROMATOGRAPHY; TURNOVER TIME;

EID: 0042497321     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390002     Document Type: Conference Paper

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114. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
115. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
116. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
117. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
118. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
119. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
120. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
121. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
122. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
123. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
124. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
125. For early efforts, see: a) J. Solodar, CHEMTECH 1975, 5, 421; b) T. Hayashi, T. Mise, M. Kumada, Tetrahedron Lett. 1976, 4351; c) S. Torös, B. Heil, L. Kollár, L. Markó, J. Organomet. Chem. 1980, 197, 85; d) J. Bakos, I. Tóth, B. Heil, L. Markó, J. Organomet. Chem. 1985, 279, 23; e) X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318. See also: f) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol, Chem. Eur. J. 1997, 3, 1365; g) U. Nagel, C. Roller, Z. Naturforsch. B 1998, 53, 267; h) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 1998, 110, 1203; Angew. Chem. Int. Ed. 1998, 37, 1100; i) P. Cao, X. Zhang, J. Org. Chem. 1999, 64, 2127. Heterogeneous hydrogenation, see: j) T. Osawa, A. Tai, Y. Imachi, S. Takasaki in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 75; k) T. Harada, T. Osawa in Chiral Reactions in Heterogeneous Catalysis (Eds.: G. Jannes, V. Dubois), Plenum, New York, 1995, p. 83.
126. T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675.
127. R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40.
128. R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40.
129. R. Noyori, T. Ohkuma, Pure Appl. Chem. 1999, 71, 1493.
130. R. Noyori, M. Koizumi, D. Ishii, T. Ohkuma, Pure Appl. Chem. 2001, 73, 227.
131. Abbreviations: TolBINAP = 2,2′-Bis(di-4-tolylphosphano)-1,1′- binaphthyl. XylBINAP = 2,2′-Bis(di-3,5-xylylphosphano)-1,1′- binaphthyl. DPEN = 1,2-Diphenylethylenediamine. DAIPEN = 1,1-Di-4-anisyl-2- isopropyl-1,2-ethylenediamine.
132. T. Ohkuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1998, 120, 13529.
133. T. Ohkuma, H. Ooka, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 10417.
134. T. Ohkuma, H. Ikehira, T. Ikariya, R. Noyori, Synlett 1997, 467.
135. T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749.
136. T. Ohkuma, H. Ooka, M. Yamakawa, T. Ikariya, R. Noyori, J. Org. Chem. 1996, 61, 4872.
137. T. Matsumoto, T. Murayama, S. Mitsuhashi, T. Miura, Tetrahedron Lett. 1999, 40, 5043.
138. T. Ohkuma, D. Ishii, H. Takeno, R. Noyori, J. Am. Chem. Soc. 2000, 122, 6510.
139. T. Ohkuma, M. Koizumi, H. Ikehira, T. Yokozawa, R. Noyori, Org. Lett. 2000, 2, 659.
140. T. Ohkuma, H. Doucet, T. Pham, K. Mikami, T. Korenaga, M. Terada, R. Noyori, J. Am. Chem. Soc. 1998, 120, 1086.
141. T. Ohkuma, H. Takeno, Y. Honda, R. Noyori, Adv. Synth. Catal. 2001, 343, 369.
142. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
143. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
144. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
145. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
146. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
147. Review: K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, R. Angelaud, Angew. Chem. 2000, 112, 3676; Angew. Chem. Int. Ed. 2000, 39, 3532. See also: K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517; Angew. Chem. Int. Ed. 1999, 38, 495; K. Mikami, T. Korenaga, T. Ohkuma, R. Noyori, Angew. Chem. 2000, 112, 3854; Angew. Chem. Int. Ed. 2000, 39, 3707.
148. Nonlinear effects in catalysis should be investigated carefully because of the homochiral and heterochiral interaction of the chiral species present in the catalytic system. For reviews, see: a) R. Noyori, S. Suga, H. Oka, M. Kitamura, Chem. Rec. 2001, 1, 85; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Int. Ed. 1998, 37, 2922; c) D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257.
149. Nonlinear effects in catalysis should be investigated carefully because of the homochiral and heterochiral interaction of the chiral species present in the catalytic system. For reviews, see: a) R. Noyori, S. Suga, H. Oka, M. Kitamura, Chem. Rec. 2001, 1, 85; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Int. Ed. 1998, 37, 2922; c) D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257.
150. Nonlinear effects in catalysis should be investigated carefully because of the homochiral and heterochiral interaction of the chiral species present in the catalytic system. For reviews, see: a) R. Noyori, S. Suga, H. Oka, M. Kitamura, Chem. Rec. 2001, 1, 85; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Int. Ed. 1998, 37, 2922; c) D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257.
151. Nonlinear effects in catalysis should be investigated carefully because of the homochiral and heterochiral interaction of the chiral species present in the catalytic system. For reviews, see: a) R. Noyori, S. Suga, H. Oka, M. Kitamura, Chem. Rec. 2001, 1, 85; b) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088; Angew. Chem. Int. Ed. 1998, 37, 2922; c) D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257.
152. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. 1998, 110, 1792; Angew. Chem. Int. Ed. 1998, 37, 1703.
153. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. 1998, 110, 1792; Angew. Chem. Int. Ed. 1998, 37, 1703.
154. The ketone substrate reacts in an outer sphere of the coordinatively saturated 18-electron complex without interaction with the metallic center. Thus the general scheme given in Figure 1 is to be modified to some extent. For other mechanistic investigations, see: a) K. Abdur-Rashid, M. Faatz, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2001, 123, 7473; b) R. Hartmann, P. Chen, Angew. Chem. 2001, 113, 3693; Angew. Chem. Int. Ed. 2001, 40, 3581.
155. The ketone substrate reacts in an outer sphere of the coordinatively saturated 18-electron complex without interaction with the metallic center. Thus the general scheme given in Figure 1 is to be modified to some extent. For other mechanistic investigations, see: a) K. Abdur-Rashid, M. Faatz, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2001, 123, 7473; b) R. Hartmann, P. Chen, Angew. Chem. 2001, 113, 3693; Angew. Chem. Int. Ed. 2001, 40, 3581.
156. The ketone substrate reacts in an outer sphere of the coordinatively saturated 18-electron complex without interaction with the metallic center. Thus the general scheme given in Figure 1 is to be modified to some extent. For other mechanistic investigations, see: a) K. Abdur-Rashid, M. Faatz, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2001, 123, 7473; b) R. Hartmann, P. Chen, Angew. Chem. 2001, 113, 3693; Angew. Chem. Int. Ed. 2001, 40, 3581.
157. R. Noyori, M. Yamakawa, S. Hashiguchi, J. Org. Chem. 2001, 66, 7931.
158. R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97.
159. a) K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738;
160. b) I. Yamada, R. Noyori, Org. Lett. 2000, 2, 3425.
161. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997, 36, 285.
162. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997, 36, 285.
163. a) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466;
164. b) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580.
165. M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem. 2001, 113, 2900; Angew. Chem. Int. Ed. 2001, 40, 2818.
166. M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem. 2001, 113, 2900; Angew. Chem. Int. Ed. 2001, 40, 2818.
167. a) M. Suzuki, A. Yanagisawa, R. Noyori, J. Am. Chem. Soc. 1985, 107, 3348;
168. b) M. Suzuki, A. Yanagisawa, R. Noyori, J. Am. Chem. Soc. 1988, 110, 4718;
169. c) M. Suzuki, Y. Morita, H. Koyano, M. Koga, R. Noyori, Tetrahedron 1990, 46, 4809.
170. M. Suzuki, H. Koyano, Y. Morita, R. Noyori, Synlett 1989, 22.
171. This process has been used at Ono Pharmaceutical Co. for the industrial synthesis of PGs using the Corey method.
172. a) R. Noyori, M. Suzuki, Angew. Chem. 1984, 96, 854; Angew. Chem. Int. Ed. Engl. 1984, 23, 847;
173. a) R. Noyori, M. Suzuki, Angew. Chem. 1984, 96, 854; Angew. Chem. Int. Ed. Engl. 1984, 23, 847;
174. b) R. Noyori, M. Suzuki, Chemtracts: Org. Chem. 1990, 3, 173;
175. c) R. Noyori, M. Suzuki, Science 1993, 259, 44.
176. a) M. Suzuki, K. Kato, R. Noyori, Yu. Watanabe, H. Takechi, K. Matsumura, B. Långström, Y. Watanabe, Angew. Chem. 1996, 108, 366; Angew. Chem. Int. Ed. Engl. 1996, 35, 334;
177. a) M. Suzuki, K. Kato, R. Noyori, Yu. Watanabe, H. Takechi, K. Matsumura, B. Långström, Y. Watanabe, Angew. Chem. 1996, 108, 366; Angew. Chem. Int. Ed. Engl. 1996, 35, 334;
178. b) H. Takechi, K. Matsumura, Yu. Watanabe, K. Kato, R. Noyori, M. Suzuki, Y. Watanabe, J. Biol. Chem. 1996, 271, 5901.
179. Account: M. Suzuki, R. Noyori, B. Långström, Y. Watanabe, Bull. Chem. Soc. Jpn. 2000, 73, 1053.
180. Yu. Watanabe, K. Matsumura, H. Takechi, K. Kato, H. Morii, M. Björkman, B. Långström, R. Noyori, M. Suzuki, Y. Watanabe, J. Neurochem. 1999, 72, 2583.
181. a) M. Suzuki, H. Doi, M. Björkman, Y. Andersson, B. Långström, Y. Watanabe, R. Noyori, Chem. Eur. J. 1997, 3, 2039;
182. b) M. Suzuki, H. Doi, K. Kato, M. Björkman, B. Långström, Y. Watanabe, R. Noyori, Tetrahedron 2000, 56, 8263.
183. T. Satoh, Y. Ishikawa, Y. Kataoka, Y. Cui, H. Yanase, K. Kato, Yu. Watanabe, K. Nakadate, K. Matsumura, H. Hatanaka, K. Kataoka, R. Noyori, M. Suzuki, Y. Watanabe, Eur. J. Neurosci. 1999, 11, 3115.
184. R. Noyori, S. Hashiguchi, T. Yamano in Applied Homogeneous Catalysis by Organometallic Complexes, 2nd ed. (Eds.: B. Cornus, W. A. Hermann), VCH-Wiley, Weinheim, 557.
185. Nobel lecture: K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
186. Nobel lecture: K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135; Angew. Chem. Int. Ed. 2002, 41, 2024-2032.